Hotwire has built a successful company on the element of travel surprise, letting travelers book hotels at discounted rates, and finding out which hotel they’ll be staying at after they’ve booked. Startup GetGoing is looking to bring that same element of surprise to air travel, but instead of finding out which airline they’ll be flying on, passengers choose two destinations and learn which one is confirmed after they’ve booked, in return getting discounts of up to 40 percent on fares.

The San Francisco-based startup is targeting leisure travelers who have more flexibility, rather than business travelers or anyone who has to be in a specific location at a specific time. Travelers choose the airport they want to fly out of, with more than 10 departure cities currently supported including Los Angeles, Boston, and New York City (they plan to expand to international destinations this year). Then they pick a region they want to travel to, for example the U.S. and Canada, or Africa and the Middle East, or from a category of trips like sun destinations or outdoor adventures, or a list of their own destinations. They then specify the exact dates they want to travel, and how many people are in their group.

GetGoing brings back search results for destinations in that area, with thousands of destinations in 50 countries supported, grouping flights to each city into one block. Users then pick specific flights for two of those destinations (choosing departure and arrival times and the number of layovers), for example Shanghai and Mumbai if they were looking to travel to Asia, with each flight showing passengers how much they’re saving vs. the lowest published price on other websites, which users can compare to sites like Expedia and Kayak directly on GetGoing. After confirming the details of both flights and entering their address and payment information, travelers get an email outlining which flight is confirmed (the destination is chosen randomly, what they call a “digital flip of the coin”), and the specific airline details and times.

Co-founder and CEO Alek Vernitsky said he traveled a lot growing up, both for work and for fun, and it was while traveling for business that the idea for GetGoing occurred to him. “I always wanted to make travel easier and cheaper for people,” he said in an interview. “When I was working in New York and I would fly for business I would see all these empty seats, and I was thinking to myself is there a way to sell these empty seats the airlines are not able to sell at a discount to people who can’t afford to fly, and we found a way to do it.”

The site has been in private beta for the last three months, and Vernitsky said that while he originally thought it would be used by college students and younger travelers, the audience has been students, families with young kids, and retirees.

The “pick two, get one” platform is certainly designed for ultra-flexible travelers who either don’t care which city they visit, or have some flexibility. It’s not for firm travelers, or those who want to be able to cancel, since all flights booked are non-refundable and don’t allow changes or transfers. Nor is it for people who fly a specific airline to get the rewards points, since travelers don’t find out which airline they’re flying until after they’ve booked. The company also doesn’t provide one-way flights, only booking round-trip tickets, and only sells economy tickets, not first class.

Vernitsky is hoping the lower fares will make travelers forget about those issues. The company works directly with over 10 domestic and international airlines to get discounted fares, which they said airlines are more willing to give to flexible leisure travelers since they’re typically more concerned about price than business travelers. He said the airlines don’t just want to discount the flights themselves because they don’t want to discount for business travelers who can pay more.

“Once you discount the flight, you’ve discounted it to everybody, not just to people who can’t afford to fly, but also to people who were about to pay full price,” he said. “Effectively we are able to target the seats that the airlines have not been able to sell, and the discounts, just to the people who can’t afford to pay or don’t want to pay full price.

So are the discounts worth it? Vernitsky says consumers can get up to 40 percent off fares by booking through GetGoing. The company also has a 24-hour price guarantee, so if someone books a flight and finds the exact same itinerary for a cheaper price on another website, GetGoing refunds the difference. For a trip to Shanghai leaving from San Francisco’s SFO airport on April 1st and returning on April 8th, the cheapest listed flight on Expedia is $1,019. The cheapest flight on GetGoing is $808, and based on the departure times, it looks like that could be the same flight (though a user wouldn’t know until they booked) for over $200 cheaper. But obviously there’s no guarantee a user would get that flight vs. another Asian destination like Manila or Seoul.

The company plans to add hotel bookings and prepackaged vacations in the next couple months, which will put it into direct competition with other discount hotel booking sites like Priceline, Hotwire, and Expedia. It also has to compete with other startups that are using innovative methods to save travelers money on air travel, like Steadyfare, which lets travelers book in low prices now and book later for a fee, or Flightfox, which lets local experts find cheaper flight options for travelers. A Y Combinator grad with backing from Lightbank and TA Venture among other investors, GetGoing has the partnerships and backing in place to make it successful. But whether it will catch on with its most important target audience, leisure travelers, is another question entirely, since though leisure travelers might be more flexible, they may not be willing to leave their destination up to chance.

Erin Bury is the Managing Director at 88 Creative, a creative communications agency based in Toronto. She was formerly the Managing Editor at BetaKit, and currently writes a monthly column for the Financial Post. Follow her on Twitter at @erinbury.